Hydrochloric Acid → HCID 14500663, compound

HRID 1761601Notes

Reaction equation

HRID 1761601 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][CH:6]=[C:5]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]([NH2:19])=[O:18])[CH:11]=1)[CH2:2][CH3:3].Cl>O.CO>[CH2:1]([N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]([NH2:19])=[O:18])[CH:11]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14500641HCID 14500641, compound

Product 1

HCID 14500663HCID 14500663, compoundYield 54.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1-Propyl-2-(3'-ureidobenzyl)pyrrole 2 g (7.7 mmol), prepared, for example, as described in Preparation 5D, was suspended in 80 ml of water and 20 ml of a 1.044M solution of hydrochloric acid (20 mmol) in methanol. This suspension was hydrogenated at 45 p.s.i. in the presence of 1.45 g of 5% rodium on activated alumina as catalyst, for 1 hour. The catalyst was then separated by filtration and the filtrate evaporated in vacuo. The aqueous residue was treated with ammonium hydroxide until an alkaline pH was obtained, and the product extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (2×50 ml), dried over sodium sulfate and evaporated under reduced pressure. The residue was crystallized from ethanol-water, thus obtaining 1.1 g (54%) of 1-propyl-2-(3'-ureidobenzyl)pyrrolidine, the title compound. M.P. 101°-104° C.

Workup

  1. customThe catalyst was then separated by filtration
  2. customthe filtrate evaporated in vacuo
  3. additionThe aqueous residue was treated with ammonium hydroxide until an alkaline pH
  4. customwas obtained
  5. extractionthe product extracted with ethyl acetate (3×100 ml)
  6. washThe combined extracts were washed with water (2×50 ml)
  7. dry with materialdried over sodium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was crystallized from ethanol-water

Sources & evidence

ORD record
ord-2a34e58f59e94cb0b7328e86317a93af
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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